CH495996A - Verfahren zur Herstellung von Nitroimidazolderivaten - Google Patents

Verfahren zur Herstellung von Nitroimidazolderivaten

Info

Publication number: CH495996A
Authority: CH; Switzerland
Prior art keywords: nitro; nitrophenyl; formula; methyl; nitroimidazole
Prior art date: 1966-10-15

Application number

CH1107067A

Other languages

German (de)

English (en)

Inventor

Rainer Dr Klink

Ludwig Dr Hepding

Original Assignee

Merck Ag E

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1966-10-15

Filing date

1967-08-04

Publication date

1970-09-15

1967-08-04 Application filed by Merck Ag E filed Critical Merck Ag E

1970-09-15 Publication of CH495996A publication Critical patent/CH495996A/de

Links

-1 1-nitropyridyl Chemical group 0.000 title description 18
241001502500 Trichomonadida Species 0.000 title description 3
125000006501 nitrophenyl group Chemical group 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
VYDWQPKRHOGLPA-UHFFFAOYSA-N 5-nitroimidazole Chemical compound [O-][N+](=O)C1=CN=CN1 VYDWQPKRHOGLPA-UHFFFAOYSA-N 0.000 claims description 7
150000004820 halides Chemical class 0.000 claims description 7
238000000034 method Methods 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
150000004957 nitroimidazoles Chemical class 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
229940058965 antiprotozoal agent against amoebiasis and other protozoal diseases nitroimidazole derivative Drugs 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000003385 sodium Chemical class 0.000 claims 1
FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 abstract description 3
CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 abstract description 3
241000224527 Trichomonas vaginalis Species 0.000 abstract description 3
210000003754 fetus Anatomy 0.000 abstract description 3
241000224432 Entamoeba histolytica Species 0.000 abstract description 2
241000223107 Trypanosoma congolense Species 0.000 abstract description 2
241000223089 Trypanosoma equiperdum Species 0.000 abstract description 2
241000223095 Trypanosoma evansi Species 0.000 abstract description 2
229940007078 entamoeba histolytica Drugs 0.000 abstract description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract description 2
241000893962 Trichophyton equinum Species 0.000 abstract 1
230000001572 anti-trichomonad Effects 0.000 abstract 1
125000004076 pyridyl group Chemical group 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000000243 solution Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
QLHVJBXAQWPEDI-UHFFFAOYSA-N 2-chloro-3,5-dinitropyridine Chemical class [O-][N+](=O)C1=CN=C(Cl)C([N+]([O-])=O)=C1 QLHVJBXAQWPEDI-UHFFFAOYSA-N 0.000 description 3
BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 2
XUCYJGMIICONES-UHFFFAOYSA-N 1-fluoro-2-methyl-4-nitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1F XUCYJGMIICONES-UHFFFAOYSA-N 0.000 description 2
PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 2
WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 2
UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 2
241000224526 Trichomonas Species 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 2
NMTBSNPBIGRZBL-UHFFFAOYSA-N nitrefazole Chemical compound CC1=NC([N+]([O-])=O)=CN1C1=CC=C([N+]([O-])=O)C=C1 NMTBSNPBIGRZBL-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
DJNPMCYHIMPXIT-UHFFFAOYSA-N 1-(2,4-dinitrophenyl)-2-methyl-4-nitroimidazole Chemical compound CC1=NC([N+]([O-])=O)=CN1C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O DJNPMCYHIMPXIT-UHFFFAOYSA-N 0.000 description 1
QXWPSFKPIHTHPL-UHFFFAOYSA-N 1-(2,4-dinitrophenyl)-4-nitroimidazole Chemical compound C1=NC([N+](=O)[O-])=CN1C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O QXWPSFKPIHTHPL-UHFFFAOYSA-N 0.000 description 1
ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
ZDFBKZUDCQQKAC-UHFFFAOYSA-N 1-bromo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1 ZDFBKZUDCQQKAC-UHFFFAOYSA-N 0.000 description 1
NWAOUFGCGKRZBR-UHFFFAOYSA-N 1-chloro-2,3-dimethyl-4-nitrobenzene Chemical group CC1=C(C)C([N+]([O-])=O)=CC=C1Cl NWAOUFGCGKRZBR-UHFFFAOYSA-N 0.000 description 1
JMEXAQBBMDHIGQ-UHFFFAOYSA-N 1-chloro-2,5-dimethyl-4-nitrobenzene Chemical group CC1=CC([N+]([O-])=O)=C(C)C=C1Cl JMEXAQBBMDHIGQ-UHFFFAOYSA-N 0.000 description 1
BGDCQZFFNFXYQC-UHFFFAOYSA-N 1-chloro-2-methyl-4-nitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1Cl BGDCQZFFNFXYQC-UHFFFAOYSA-N 0.000 description 1
KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 1
PXPMXGBWFXMDTR-UHFFFAOYSA-N 1-chloro-4-(2-nitroethyl)benzene Chemical compound [O-][N+](=O)CCC1=CC=C(Cl)C=C1 PXPMXGBWFXMDTR-UHFFFAOYSA-N 0.000 description 1
LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 1
WMASLRCNNKMRFP-UHFFFAOYSA-N 1-fluoro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(F)=C1 WMASLRCNNKMRFP-UHFFFAOYSA-N 0.000 description 1
JXMZUNPWVXQADG-UHFFFAOYSA-N 1-iodo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1I JXMZUNPWVXQADG-UHFFFAOYSA-N 0.000 description 1
SCCCFNJTCDSLCY-UHFFFAOYSA-N 1-iodo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(I)C=C1 SCCCFNJTCDSLCY-UHFFFAOYSA-N 0.000 description 1
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
JHFOWEGCZWLHNW-UHFFFAOYSA-N 4-fluoro-2-methyl-1-nitrobenzene Chemical compound CC1=CC(F)=CC=C1[N+]([O-])=O JHFOWEGCZWLHNW-UHFFFAOYSA-N 0.000 description 1
PGGLEPBDEDPURO-UHFFFAOYSA-N 4-nitro-1-(4-nitrophenyl)imidazole Chemical compound C1=NC([N+](=O)[O-])=CN1C1=CC=C([N+]([O-])=O)C=C1 PGGLEPBDEDPURO-UHFFFAOYSA-N 0.000 description 1
WDJJMYKUUPSSBL-UHFFFAOYSA-N 5-nitro-2-(4-nitroimidazol-1-yl)pyridine Chemical compound [N+](=O)([O-])C=1C=CC(=NC1)N1C=NC(=C1)[N+](=O)[O-] WDJJMYKUUPSSBL-UHFFFAOYSA-N 0.000 description 1
208000006503 Amebic Liver Abscess Diseases 0.000 description 1
241000224489 Amoeba Species 0.000 description 1
206010001986 Amoebic dysentery Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000224421 Heterolobosea Species 0.000 description 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000699673 Mesocricetus auratus Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000223104 Trypanosoma Species 0.000 description 1
GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
YHXRKRUYLZTNJE-UHFFFAOYSA-N [N+](=O)([O-])C=1C=CC(=NC1)N1C(=NC(=C1)[N+](=O)[O-])C Chemical compound [N+](=O)([O-])C=1C=CC(=NC1)N1C(=NC(=C1)[N+](=O)[O-])C YHXRKRUYLZTNJE-UHFFFAOYSA-N 0.000 description 1
206010000269 abscess Diseases 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
210000003001 amoeba Anatomy 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
230000035876 healing Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000002641 lithium Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
206010034674 peritonitis Diseases 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

CH1107067A 1966-10-15 1967-08-04 Verfahren zur Herstellung von Nitroimidazolderivaten CH495996A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE1620043A DE1620043C3 (de)	1966-10-15	1966-10-15	1 -(p-Nitrophenyl)-4-nitroimidazole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DEM0072966		1967-03-01

Publications (1)

Publication Number	Publication Date
CH495996A true CH495996A (de)	1970-09-15

Family

ID=25987949

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1107067A CH495996A (de)	1966-10-15	1967-08-04	Verfahren zur Herstellung von Nitroimidazolderivaten
CH1800269A CH487899A (de)	1966-10-15	1967-08-04	Verfahren zur Herstellung von Nitroimidazolderivaten

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1800269A CH487899A (de)	1966-10-15	1967-08-04	Verfahren zur Herstellung von Nitroimidazolderivaten

Country Status (11)

Country	Link
US (1)	US3491105A (fr)
BE (1)	BE705082A (fr)
CH (2)	CH495996A (fr)
DE (2)	DE1620043C3 (fr)
DK (1)	DK125891B (fr)
ES (1)	ES346075A1 (fr)
FR (1)	FR7260M (fr)
GB (1)	GB1133408A (fr)
IL (1)	IL28550A (fr)
NL (1)	NL155543B (fr)
YU (1)	YU34239B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2522176A1 (de) *	1975-05-17	1976-11-25	Hoechst Ag	1-methyl-2-(pyridyl-oxymethyl)-nitro- imidazole und verfahren zu ihrer herstellung
US4182770A (en)	1976-10-09	1980-01-08	Merck Patent Gesellschaft Mit Beschraenkter Haftung	Alcohol deterrent
DE2645709C2 (de) *	1976-10-09	1985-04-25	Merck Patent Gmbh, 6100 Darmstadt	Verwendung von 1-(4-Nitrophenyl)-2-methyl-4-nitroimidazol bei der Erzielung einer Aversion gegen Alkohol
ZA826043B (en) *	1981-08-21	1983-07-27	May & Baker Ltd	Control of industrial spoilage with nitroimidazole compounds
US5855902A (en) *	1992-11-02	1999-01-05	Protatek International, Inc.	Method of administering a vaccine comprising tritrichomonas foetus membrane surface antigens between 45 and 300 kilopaltons

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3065133A (en) *	1956-09-28	1962-11-20	Rhone Poulenc Sa	Imidazoles for the control of histomoniasis
US3255201A (en) *	1965-04-09	1966-06-07	Hoffmann La Roche	2-nitroimidazoles

1966
- 1966-10-15 DE DE1620043A patent/DE1620043C3/de not_active Expired
1967
- 1967-03-01 DE DE19671695397 patent/DE1695397A1/de active Pending
- 1967-08-04 CH CH1107067A patent/CH495996A/de not_active IP Right Cessation
- 1967-08-04 CH CH1800269A patent/CH487899A/de not_active IP Right Cessation
- 1967-08-21 NL NL6711502.A patent/NL155543B/xx not_active IP Right Cessation
- 1967-08-22 GB GB38544/67A patent/GB1133408A/en not_active Expired
- 1967-08-23 IL IL28550A patent/IL28550A/en unknown
- 1967-09-12 FR FR120723A patent/FR7260M/fr not_active Expired
- 1967-09-22 DK DK473067AA patent/DK125891B/da unknown
- 1967-09-25 US US670414A patent/US3491105A/en not_active Expired - Lifetime
- 1967-10-13 BE BE705082D patent/BE705082A/xx not_active IP Right Cessation
- 1967-10-14 ES ES346075A patent/ES346075A1/es not_active Expired
1970
- 1970-04-30 YU YU1113/70A patent/YU34239B/xx unknown

Also Published As

Publication number	Publication date
DK125891B (da)	1973-05-21
GB1133408A (en)	1968-11-13
FR7260M (fr)	1969-09-15
NL155543B (nl)	1978-01-16
CH487899A (de)	1970-03-31
IL28550A (en)	1971-10-20
US3491105A (en)	1970-01-20
DE1620043A1 (de)	1970-03-19
BE705082A (fr)	1968-04-16
DE1695397A1 (de)	1971-03-18
YU34239B (en)	1979-04-30
ES346075A1 (es)	1969-03-16
DE1620043B2 (de)	1978-06-01
NL6711502A (fr)	1968-04-16
YU111370A (en)	1978-10-31
DE1620043C3 (de)	1979-02-15

Legal Events

Date	Code	Title	Description
1986-04-30	PL	Patent ceased

Publication	Publication Date	Title
DE1620442C3 (de)	1975-07-03	Verfahren zur Herstellung von 1-Acylindolverbindungen
DE2052692A1 (de)	1971-05-06	Isothioharnstoffverbmdungen, ihre Salze mit Sauren, Verfahren zu ihrer Her stellung und ihre Verwendung zur Her stellung von Arzneimitteln
DE2921660A1 (de)	1980-01-10	5-nitroimidazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende antiprotozoen-mittel
DE1695656B2 (de)	1974-06-06	l-Alkyl-4-aryl-2(lH)-chinazoIinone
DE2247186A1 (de)	1974-03-28	Antimykotisches mittel
DE1620043C3 (de)	1979-02-15	1 -(p-Nitrophenyl)-4-nitroimidazole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2931735A1 (de)	1981-02-19	Neue substituierte phenylacetylguanidine und verfahren zu ihrer herstellung
DE2917244A1 (de)	1979-11-22	4'-substituierte 2,4-dichlor- alpha (imidazol-n-ylmethyl)-dibenzylaether, verfahren zu deren herstellung sowie solche enthaltende arzneimittel
DE1670097A1 (de)	1972-03-02	Indolyltetrazolderivate und Verfahren zu ihrer Herstellung
DE1931061A1 (de)	1970-01-08	Pyrazolverbindungen,Verfahren zu ihrer Herstellung und ihre Verwendung
DE1695804C3 (de)	1973-10-25	N Acyl 2 methyl 3 lndolylcarbon sauren, Verfahren zu ihrer Herstellung und Arzneimittel
CH474490A (de)	1969-06-30	Verfahren zur Herstellung neuer Benzolsulfonylharnstoffe
DE1960026A1 (de)	1971-06-03	Neue Derivate des 3-Amino-1,2-benzisothiazols und ein Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
AT296316B (de)	1972-02-10	Verfahren zur Herstellung von neuen Benzodiazepin-Derivaten und deren N-4-Oxyden
AT211307B (de)	1960-10-10	Verfahren zur Herstellung von neuen N-(5-Nitro-2-furfuryliden)-amino- heterocyclen
DE1695748C3 (de)	1974-07-25	l-Acyl^-methyl-S-methoxyindolylessigsäuren. Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
AT274808B (de)	1969-10-10	Verfahren zur Herstellung von Imidazolderivaten
AT274801B (de)	1969-10-10	Verfahren zur Herstellung von neuen 1-Acyl-3-indolylcarbonsäureverbindungen
DE1620726C (de)	1973-07-05	1 substituierte Monomtroimidazole, ihre Herstellung und Verwendung
AT314530B (de)	1974-04-10	Verfahren zur Herstellung von neuen 5- bzw. 4-Nitroimidazolderivaten und ihren Salzen
AT278808B (de)	1970-02-10	Verfahren zur Herstellung neuer 4-Acyl-3,4-dihydro-2(1H)-chinoxalinonderivate
DE2700346A1 (de)	1977-07-28	2-nitroimidazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
AT225188B (de)	1963-01-10	Verfahren zur Herstellung von neuen, in 3-Stellung substituierten Derivaten des 1-(5-Nitrofurfuryliden-amino)-hydantoins
AT201059B (de)	1958-12-10	Verfahren zur Herstellung von neuen 3,5-Diketo-pyrazolidinderivaten
DE3409403A1 (de)	1985-09-26	Lipoxygenasehemmendes arzneimittel